Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 # Attachment 'Desiraju_Submit_CIF_27_June.cif' # SUBMISSION DETAILS _publ_contact_author_name 'Professor Gautam R. Desiraju' _publ_contact_author_address ; School of Chemistry University of Hyderabad Hyderabad 500 046, India ; _publ_contact_author_email gautam_desiraju@yahoo.com _publ_contact_author_phone '91 40 23010500 extn. 4828' _publ_contact_author_fax '91 40 3010567' _publ_requested_journal CrystEngComm # TITLE AND AUTHOR LIST _publ_section_title ; Crystal Structure Prediction of Aminophenols with the Supramolecular Synthon Approach: Experimental Verifications ; loop_ _publ_author_name _publ_author_address 'Archan Dey' ;School of Chemistry University of Hyderabad Hyderabad 500 046, India ; 'Narendra Nath Pati' ;School of Chemistry University of Hyderabad Hyderabad 500 046, India ; 'Gautam R. Desiraju' ;School of Chemistry University of Hyderabad Hyderabad 500 046, India ; data_1 _database_code_depnum_ccdc_archive 'CCDC 612505' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-amino-4-ethylphenol ; _chemical_name_common 2-amino-4-ethylphenol _chemical_melting_point 408 _chemical_formula_moiety C8H11NO _chemical_formula_sum 'C8 H11 N O' _chemical_formula_weight 137.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.806(13) _cell_length_b 7.155(6) _cell_length_c 7.820(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.861(14) _cell_angle_gamma 90.00 _cell_volume 825.4(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 585 _cell_measurement_theta_min 3.87 _cell_measurement_theta_max 25.62 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6353 _diffrn_reflns_av_R_equivalents 0.1867 _diffrn_reflns_av_sigmaI/netI 0.1683 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1460 _reflns_number_gt 663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1099P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1460 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1872 _refine_ls_R_factor_gt 0.0806 _refine_ls_wR_factor_ref 0.2201 _refine_ls_wR_factor_gt 0.1759 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.0050(2) 0.0640(4) 0.2673(3) 0.0282(9) Uani 1 1 d . . . C1 C 0.2393(3) -0.1015(6) 0.2820(5) 0.0256(12) Uani 1 1 d . . . H1 H 0.2762 -0.1905 0.3450 0.031 Uiso 1 1 calc R . . N1 N 0.1072(3) -0.1990(5) 0.4382(4) 0.0261(11) Uani 1 1 d . . . C2 C 0.0930(3) 0.0520(6) 0.2280(5) 0.0224(11) Uani 1 1 d . . . C3 C 0.2773(3) 0.0063(6) 0.1528(5) 0.0253(12) Uani 1 1 d . . . C4 C 0.1497(3) -0.0800(6) 0.3184(4) 0.0221(11) Uani 1 1 d . . . C5 C 0.2192(3) 0.1377(6) 0.0634(5) 0.0312(13) Uani 1 1 d . . . H5 H 0.2423 0.2125 -0.0234 0.037 Uiso 1 1 calc R . . C6 C 0.1293(3) 0.1601(6) 0.0994(5) 0.0301(13) Uani 1 1 d . . . H6 H 0.0921 0.2490 0.0367 0.036 Uiso 1 1 calc R . . C7 C 0.3754(3) -0.0129(6) 0.1198(5) 0.0335(13) Uani 1 1 d . . . H7A H 0.3829 0.0265 0.0005 0.040 Uiso 1 1 calc R . . H7B H 0.3928 -0.1463 0.1303 0.040 Uiso 1 1 calc R . . C8 C 0.4396(4) 0.1020(9) 0.2421(8) 0.076(2) Uani 1 1 d . . . H8A H 0.4236 0.2346 0.2312 0.113 Uiso 1 1 calc R . . H8B H 0.5021 0.0840 0.2130 0.113 Uiso 1 1 calc R . . H8C H 0.4342 0.0610 0.3604 0.113 Uiso 1 1 calc R . . H2A H 0.154(2) -0.260(5) 0.494(5) 0.017(11) Uiso 1 1 d . . . H1A H 0.058(3) -0.117(6) 0.514(5) 0.047(13) Uiso 1 1 d . . . H3A H -0.028(3) 0.130(7) 0.191(6) 0.046(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.056(2) 0.020(2) 0.0083(15) 0.0010(13) 0.0006(15) 0.0069(16) C1 0.049(3) 0.016(3) 0.011(2) -0.0015(18) 0.001(2) 0.004(2) N1 0.051(3) 0.017(2) 0.0107(18) 0.0052(17) 0.0031(18) 0.003(2) C2 0.042(3) 0.017(3) 0.008(2) -0.0011(17) 0.0031(19) 0.003(2) C3 0.047(3) 0.016(3) 0.013(2) 0.003(2) 0.004(2) 0.000(2) C4 0.049(3) 0.012(3) 0.005(2) -0.0023(17) 0.000(2) -0.004(2) C5 0.064(4) 0.019(3) 0.012(2) 0.0039(19) 0.010(2) -0.002(2) C6 0.055(3) 0.022(3) 0.014(2) 0.0056(19) 0.007(2) 0.004(2) C7 0.059(4) 0.023(3) 0.020(2) 0.002(2) 0.007(2) 0.000(2) C8 0.069(4) 0.082(5) 0.078(4) -0.044(4) 0.021(3) -0.017(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.368(5) . ? O1 H3A 0.87(5) . ? C1 C4 1.388(6) . ? C1 C3 1.424(6) . ? C1 H1 0.9500 . ? N1 C4 1.449(5) . ? N1 H2A 0.90(4) . ? N1 H1A 1.15(4) . ? C2 C6 1.411(6) . ? C2 C4 1.413(5) . ? C3 C5 1.418(6) . ? C3 C7 1.503(6) . ? C5 C6 1.393(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.530(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H3A 112(3) . . ? C4 C1 C3 121.8(4) . . ? C4 C1 H1 119.1 . . ? C3 C1 H1 119.1 . . ? C4 N1 H2A 104(2) . . ? C4 N1 H1A 112(2) . . ? H2A N1 H1A 120(3) . . ? O1 C2 C6 123.6(4) . . ? O1 C2 C4 117.8(4) . . ? C6 C2 C4 118.5(4) . . ? C5 C3 C1 116.7(4) . . ? C5 C3 C7 122.0(4) . . ? C1 C3 C7 121.2(4) . . ? C1 C4 C2 120.6(4) . . ? C1 C4 N1 122.9(4) . . ? C2 C4 N1 116.4(4) . . ? C6 C5 C3 121.8(4) . . ? C6 C5 H5 119.1 . . ? C3 C5 H5 119.1 . . ? C5 C6 C2 120.6(4) . . ? C5 C6 H6 119.7 . . ? C2 C6 H6 119.7 . . ? C3 C7 C8 113.7(4) . . ? C3 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C3 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.283 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.076 data_2 _database_code_depnum_ccdc_archive 'CCDC 612506' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3 amino 2 naphthol ; _chemical_name_common '3 amino 2 naphthol' _chemical_melting_point 483 _chemical_formula_moiety 'C10 H9 N O' _chemical_formula_sum 'C10 H9 N O' _chemical_formula_weight 159.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.1054(13) _cell_length_b 6.0153(5) _cell_length_c 8.4629(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.5820(10) _cell_angle_gamma 90.00 _cell_volume 758.24(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2785 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 25.98 _exptl_crystal_description Block _exptl_crystal_colour 'pale brown' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4619 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 26.01 _reflns_number_total 1493 _reflns_number_gt 1388 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.3090P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1493 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1121 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.52585(6) 1.10247(16) 0.33309(10) 0.0191(3) Uani 1 1 d . . . C1 C 0.66197(8) 1.1861(2) 0.23122(14) 0.0160(3) Uani 1 1 d . . . H1 H 0.6387 1.3260 0.1920 0.019 Uiso 1 1 calc R . . C2 C 0.72953(8) 0.7743(2) 0.35138(13) 0.0155(3) Uani 1 1 d . . . H2 H 0.7521 0.6350 0.3930 0.019 Uiso 1 1 calc R . . C3 C 0.87031(8) 0.8452(2) 0.24414(15) 0.0181(3) Uani 1 1 d . . . H3 H 0.8940 0.7066 0.2853 0.022 Uiso 1 1 calc R . . C4 C 0.74936(8) 1.1203(2) 0.20747(13) 0.0153(3) Uani 1 1 d . . . C5 C 0.78336(8) 0.9111(2) 0.26850(13) 0.0152(3) Uani 1 1 d . . . C6 C 0.64544(8) 0.8409(2) 0.37207(13) 0.0148(3) Uani 1 1 d . . . C7 C 0.80303(8) 1.2550(2) 0.12356(14) 0.0177(3) Uani 1 1 d . . . H7 H 0.7809 1.3951 0.0826 0.021 Uiso 1 1 calc R . . N1 N 0.58585(7) 0.7032(2) 0.44015(12) 0.0172(3) Uani 1 1 d . . . C8 C 0.61119(8) 1.0501(2) 0.31000(13) 0.0155(3) Uani 1 1 d . . . C9 C 0.88655(8) 1.1857(2) 0.10079(15) 0.0201(3) Uani 1 1 d . . . H9 H 0.9216 1.2772 0.0436 0.024 Uiso 1 1 calc R . . C10 C 0.92060(8) 0.9787(2) 0.16211(15) 0.0204(3) Uani 1 1 d . . . H10 H 0.9786 0.9318 0.1465 0.025 Uiso 1 1 calc R . . H2A H 0.6146(11) 0.591(3) 0.4961(18) 0.026(4) Uiso 1 1 d . . . H1A H 0.4929(13) 1.134(3) 0.238(3) 0.045(5) Uiso 1 1 d . . . H3A H 0.5495(11) 0.781(3) 0.4973(19) 0.028(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0148(5) 0.0268(6) 0.0162(5) 0.0025(4) 0.0035(3) 0.0051(4) C1 0.0180(6) 0.0149(6) 0.0141(6) -0.0004(5) -0.0004(5) 0.0018(5) C2 0.0164(6) 0.0146(6) 0.0142(6) -0.0009(5) -0.0012(5) 0.0007(5) C3 0.0158(6) 0.0176(7) 0.0198(6) -0.0008(5) 0.0001(5) 0.0016(5) C4 0.0148(6) 0.0171(7) 0.0130(6) -0.0024(5) -0.0004(4) -0.0010(5) C5 0.0147(6) 0.0165(6) 0.0132(6) -0.0026(5) -0.0006(4) -0.0009(5) C6 0.0149(6) 0.0175(6) 0.0111(5) -0.0024(5) -0.0001(4) -0.0030(5) C7 0.0186(6) 0.0166(6) 0.0170(6) 0.0000(5) 0.0002(5) -0.0019(5) N1 0.0159(5) 0.0188(6) 0.0169(5) 0.0018(4) 0.0029(4) 0.0000(4) C8 0.0133(6) 0.0200(7) 0.0122(6) -0.0033(5) -0.0004(4) 0.0019(5) C9 0.0176(6) 0.0235(7) 0.0194(6) -0.0001(5) 0.0035(5) -0.0061(5) C10 0.0128(6) 0.0264(7) 0.0220(6) -0.0021(5) 0.0028(5) -0.0001(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.3722(14) . ? O1 H1A 0.89(2) . ? C1 C8 1.3685(18) . ? C1 C4 1.4242(16) . ? C1 H1 0.9500 . ? C2 C6 1.3706(16) . ? C2 C5 1.4214(17) . ? C2 H2 0.9500 . ? C3 C10 1.3710(18) . ? C3 C5 1.4194(16) . ? C3 H3 0.9500 . ? C4 C7 1.4179(17) . ? C4 C5 1.4231(18) . ? C6 N1 1.4145(16) . ? C6 C8 1.4272(18) . ? C7 C9 1.3724(18) . ? C7 H7 0.9500 . ? N1 H2A 0.893(17) . ? N1 H3A 0.917(17) . ? C9 C10 1.413(2) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O1 H1A 108.4(12) . . ? C8 C1 C4 120.68(12) . . ? C8 C1 H1 119.7 . . ? C4 C1 H1 119.7 . . ? C6 C2 C5 120.81(12) . . ? C6 C2 H2 119.6 . . ? C5 C2 H2 119.6 . . ? C10 C3 C5 120.93(12) . . ? C10 C3 H3 119.5 . . ? C5 C3 H3 119.5 . . ? C7 C4 C5 119.04(11) . . ? C7 C4 C1 122.16(12) . . ? C5 C4 C1 118.80(11) . . ? C3 C5 C2 121.94(12) . . ? C3 C5 C4 118.75(11) . . ? C2 C5 C4 119.30(11) . . ? C2 C6 N1 123.16(12) . . ? C2 C6 C8 119.85(11) . . ? N1 C6 C8 116.74(11) . . ? C9 C7 C4 120.80(12) . . ? C9 C7 H7 119.6 . . ? C4 C7 H7 119.6 . . ? C6 N1 H2A 111.8(10) . . ? C6 N1 H3A 113.3(10) . . ? H2A N1 H3A 112.6(14) . . ? C1 C8 O1 123.24(11) . . ? C1 C8 C6 120.55(11) . . ? O1 C8 C6 116.21(11) . . ? C7 C9 C10 120.23(12) . . ? C7 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C3 C10 C9 120.25(11) . . ? C3 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.185 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.060